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Green synthesis method of 2-trifluoromethylindole

A green synthesis technology of trifluoromethylindole, applied in the direction of organic chemistry, can solve the problems of unsuitable scale production, complex process, and great influence, and achieve the effect of easy scale manufacturing, simple process, and no by-products

Pending Publication Date: 2021-07-30
SINOPHARM CHEM REAGENT
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The existing synthesis technology has a great impact on the environment and is not suitable for large-scale production. The process is relatively complicated and the cost is high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] A kind of green synthesis method of 2-trifluoromethylindole, comprises the steps:

[0033] (1) Add 138g (0.526mol) of triphenylphosphine, 1.65g (0.0163mol) of triethylamine, 20.0g (0.175mol) trifluoroacetic acid and 0.212mol of o-toluidine, and stirred and mixed at 8° C. for 15 minutes; after stirring, 123.0 g of a mass fraction of 15% sodium bromide aqueous solution and 7.0 g (0.175 mol) of sodium hydroxide were added and continued Stir and mix for 15 minutes to obtain reaction solution A;

[0034] (2) The reaction solution A was heated up to 25° C., and after the temperature was raised, 150 mL of a sodium hypochlorite solution with a mass fraction of 8% was added under the irradiation of an ultraviolet lamp with a wavelength of 320 nm and stirred evenly, and the reaction solution was incubated for 30 minutes to obtain the reaction solution B;

[0035] (3) Warm up the reaction liquid B to reflux, react for 120 minutes, cool to room temperature after the reaction, and ...

Embodiment 2

[0045] A kind of green synthesis method of 2-trifluoromethylindole, comprises the steps:

[0046] (1) Add 130g (0.496mol) of triphenylphosphine, 1.01g (0.01mol) of triethylamine, 20.3g (0.178mol) trifluoroacetic acid and 0.182mol of o-toluidine, and stirred and mixed at 5° C. for 20 minutes; after stirring, 123.0 g of a mass fraction of 10% sodium bromide aqueous solution and 9.9 g (0.248 mol) of sodium hydroxide were added and continued Stir and mix for 15 minutes to obtain reaction solution A;

[0047] (2) Raise the temperature of the above reaction solution A to 30°C, add 200mL of sodium hypochlorite solution with a mass fraction of 5% under the irradiation of an ultraviolet lamp with a wavelength of 280nm after the temperature rise and stir evenly, and keep the reaction for 20 minutes to obtain the reaction solution B ;

[0048] (3) The resulting reaction solution B was heated to reflux, reacted for 100 minutes, cooled to room temperature after the reaction, and then sep...

Embodiment 3

[0056] A kind of green synthesis method of 2-trifluoromethylindole, comprises the steps:

[0057] (1) Add 146g (0.557mol) of triphenylphosphine, 2.73g (0.027mol) of triethylamine, 19.1g (0.168mol) trifluoroacetic acid and 0.238mol of o-toluidine, and stirred and mixed at 10° C. for 10 minutes; after stirring, 123.0 g of a mass fraction of 20% sodium bromide aqueous solution and 4.52 g (0.113 mol) of sodium hydroxide were added and continued Stir and mix for 15 minutes to obtain reaction solution A;

[0058] (2) Raise the temperature of the above reaction solution A to 25°C, add 200mL of sodium hypochlorite solution with a mass fraction of 10% under the irradiation of an ultraviolet lamp with a wavelength of 300nm after the temperature rise and stir evenly, and keep the reaction for 40 minutes to obtain the reaction solution B ;

[0059] (3) The resulting reaction solution B is heated to reflux, reacted for 80 minutes, cooled to room temperature after the reaction, and then s...

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Abstract

The invention discloses a green synthesis method of 2-trifluoromethylindole, which comprises the following steps: (1) mixing EDC, triphenylphosphine, triethylamine, trifluoroacetic acid, o-toluidine, a sodium bromide solution and alkali to obtain a reaction solution A; (2) conducting heating, conducting irradiating with an ultraviolet lamp, and adding a sodium hypochlorite solution to obtain a reaction solution B; (3) refluxing the reaction liquid B, conducting cooling and splitting phases to obtain a water phase I and an organic phase I; (4) extracting the water phase I with EDC to obtain an extracting solution; (5) filtering the organic phase I, and washing a filter cake with EDC to obtain a washing solution; (6) mixing the extracting solution, the filtrate and the washing solution, and conducting washing and drying to obtain a mixed solution; (7) conducting desolventizing and distilling to obtain a white intermediate; (8) dissolving the intermediate into a reaction solution C, then enabling a formed solution to flow through a magnesium fixed bed, conducting cooling after reaction, and adding an ammonium chloride aqueous solution for hydrolysis and phase separation to obtain a water phase II and an organic phase II; and (9) adding salt into the water phase II for saturation, conducting extracting with an organic solvent, mixing the extract and the organic phase II, and conducting washing, drying, desolventizing and crystallizing to obtain the product.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a green synthesis method of 2-trifluoromethyl indole; the synthesis method of the invention has the characteristics of high efficiency and low pollution, and is a green and environment-friendly synthesis process. Background technique [0002] Indole derivatives such as tryptophan and its metabolites, indole alkaloids, etc. are widely distributed in nature, and they provide the main framework of compounds for the discovery and development of new biologically active compounds. Studies have found that indole derivatives have various important biological activities, and the indole molecular skeleton plays an important role in the synthesis of various new drugs. For example, the indole acetic acid drug indomethacin is a non-steroidal anti-inflammatory drug, which has anti-inflammatory, antipyretic and analgesic effects; cyclomazindole and clomizindole can suppress appetite and reduce...

Claims

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Application Information

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IPC IPC(8): C07D209/10
CPCC07D209/10
Inventor 郭建国吕文华吴孝兰孙蔚晨
Owner SINOPHARM CHEM REAGENT
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